NP-MRD: Showing NP-Card for (1s)-1-[(1r,3ar,3bs,7s,9ar,9br,11r,11as)-3a,3b,7,11-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]ethyl (2e)-3-phenylprop-2-enoate (NP0262284)

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Record Information

Version

2.0

Created at

2022-09-08 05:00:32 UTC

Updated at

2022-09-08 05:00:32 UTC

NP-MRD ID

NP0262284

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s)-1-[(1r,3ar,3bs,7s,9ar,9br,11r,11as)-3a,3b,7,11-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]ethyl (2e)-3-phenylprop-2-enoate

Description

(1s)-1-[(1r,3ar,3bs,7s,9ar,9br,11r,11as)-3a,3b,7,11-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]ethyl (2e)-3-phenylprop-2-enoate is found in Cynanchum caudatum.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082207002D          

 36 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309082207002D          

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    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 14  2  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 19 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 14 35  1  0  0  0  0
 17 35  1  0  0  0  0
 35 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0262284

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](OC(=O)\C=C\C1=CC=CC=C1)[C@@H]1CC[C@@]2(O)[C@]1(C)[C@H](O)C[C@@H]1[C@@]3(C)CC[C@H](O)CC3=CC[C@@]21O

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O6/c1-19(36-26(33)10-9-20-7-5-4-6-8-20)23-13-16-30(35)28(23,3)25(32)18-24-27(2)14-12-22(31)17-21(27)11-15-29(24,30)34/h4-11,19,22-25,31-32,34-35H,12-18H2,1-3H3/b10-9+/t19-,22-,23-,24+,25+,27-,28-,29-,30+/m0/s1

> <INCHI_KEY>
BPTWUMQKPBIGJX-WEWFRUMZSA-N

> <FORMULA>
C30H40O6

> <MOLECULAR_WEIGHT>
496.644

> <EXACT_MASS>
496.282489008

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.38735809431688

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S)-1-[(1R,2R,5S,10S,11R,14R,15S,16R)-5,10,11,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethyl (2E)-3-phenylprop-2-enoate

> <JCHEM_LOGP>
3.0921989620000008

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.198018058500306

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.005859394751418

> <JCHEM_PKA_STRONGEST_BASIC>
-1.397242698663399

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
138.69320000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-1-[(1R,2R,5S,10S,11R,14R,15S,16R)-5,10,11,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethyl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.257  -5.652   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.892  -8.295   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.159  -7.873   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.685  -7.663   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.630  -8.878   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.155  -8.668   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.736  -7.241   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.791  -6.025   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.265  -6.236   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.725  -1.551   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.736  -7.323   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    2   15   35                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   35                                             
CONECT   18   17                                                            
CONECT   19   17   20   21   31                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   23   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   19   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   14   17   36                                             
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₀O₆

Average Mass

496.6440 Da

Monoisotopic Mass

496.28249 Da

IUPAC Name

(1S)-1-[(1R,2R,5S,10S,11R,14R,15S,16R)-5,10,11,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethyl (2E)-3-phenylprop-2-enoate

Traditional Name

(1S)-1-[(1R,2R,5S,10S,11R,14R,15S,16R)-5,10,11,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethyl (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

C[C@H](OC(=O)\C=C\C1=CC=CC=C1)[C@@H]1CC[C@@]2(O)[C@]1(C)[C@H](O)C[C@@H]1[C@@]3(C)CC[C@H](O)CC3=CC[C@@]21O

InChI Identifier

InChI=1S/C30H40O6/c1-19(36-26(33)10-9-20-7-5-4-6-8-20)23-13-16-30(35)28(23,3)25(32)18-24-27(2)14-12-22(31)17-21(27)11-15-29(24,30)34/h4-11,19,22-25,31-32,34-35H,12-18H2,1-3H3/b10-9+/t19-,22-,23-,24+,25+,27-,28-,29-,30+/m0/s1

InChI Key

BPTWUMQKPBIGJX-WEWFRUMZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cynanchum caudatum	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.09	ChemAxon
pKa (Strongest Acidic)	13.01	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	138.69 m³·mol⁻¹	ChemAxon
Polarizability	55.39 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s)-1-[(1r,3ar,3bs,7s,9ar,9br,11r,11as)-3a,3b,7,11-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]ethyl (2e)-3-phenylprop-2-enoate (NP0262284)

MOL for NP0262284 ((1s)-1-[(1r,3ar,3bs,7s,9ar,9br,11r,11as)-3a,3b,7,11-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]ethyl (2e)-3-phenylprop-2-enoate)

3D MOL for NP0262284 ((1s)-1-[(1r,3ar,3bs,7s,9ar,9br,11r,11as)-3a,3b,7,11-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]ethyl (2e)-3-phenylprop-2-enoate)

3D SDF for NP0262284 ((1s)-1-[(1r,3ar,3bs,7s,9ar,9br,11r,11as)-3a,3b,7,11-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]ethyl (2e)-3-phenylprop-2-enoate)

3D-SDF for NP0262284 ((1s)-1-[(1r,3ar,3bs,7s,9ar,9br,11r,11as)-3a,3b,7,11-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]ethyl (2e)-3-phenylprop-2-enoate)

PDB for NP0262284 ((1s)-1-[(1r,3ar,3bs,7s,9ar,9br,11r,11as)-3a,3b,7,11-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]ethyl (2e)-3-phenylprop-2-enoate)

3D PDB for NP0262284 ((1s)-1-[(1r,3ar,3bs,7s,9ar,9br,11r,11as)-3a,3b,7,11-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]ethyl (2e)-3-phenylprop-2-enoate)

SMILES for NP0262284 ((1s)-1-[(1r,3ar,3bs,7s,9ar,9br,11r,11as)-3a,3b,7,11-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]ethyl (2e)-3-phenylprop-2-enoate)

INCHI for NP0262284 ((1s)-1-[(1r,3ar,3bs,7s,9ar,9br,11r,11as)-3a,3b,7,11-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]ethyl (2e)-3-phenylprop-2-enoate)

Structure for NP0262284 ((1s)-1-[(1r,3ar,3bs,7s,9ar,9br,11r,11as)-3a,3b,7,11-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]ethyl (2e)-3-phenylprop-2-enoate)

3D Structure for NP0262284 ((1s)-1-[(1r,3ar,3bs,7s,9ar,9br,11r,11as)-3a,3b,7,11-tetrahydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]ethyl (2e)-3-phenylprop-2-enoate)